Remarkably efficient synthesis of 2H-indazole 1-oxides and 2H-indazoles via tandem carbon-carbon followed by nitrogen-nitrogen bond formation.
Base-catalyzed tandem carbon-carbon followed by nitrogen-nitrogen bond formations quantitatively converted N-alkyl-2-nitro-N-(2-oxo-2-aryl-ethyl)-benzenesulfonamides to 2H-indazoles 1-oxides under mild conditions. Triphenylphosphine or mesyl chloride/triethylamine-mediated deoxygenation afforded 2H-indazoles.
Bouillon
Isabelle
I
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Zajícek
Jaroslav
J
Pudelová
Nadĕzda
N
Krchnák
Viktor
V
D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D007191:Indazoles / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D009578:Nitrobenzenes / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry
D000588:Amines; D007191:Indazoles; D007659:Ketones; D009578:Nitrobenzenes; D010087:Oxides; D013449:Sulfonamides; D002244:Carbon; C036077:nitrobenzene; D009584:Nitrogen